


Up All Night to Get Lucky

by WinterWolf610



Series: Lucky [2]
Category: Supernatural
Genre: AU, Anal Sex, Barebacking, Bi Dean, Bisexual Dean, Bottom Cas, Bottom Castiel, Bottom Dean, Cock Ring, Dirty Talk, Doctor Castiel, Entirely consensual, Established Relationship, Happy Ending, Hickeys, Human Castiel, Light Spanking, M/M, Mechanic Dean, Multiple Orgasms, Oral Sex, Restraints, Sex Toys, Smut, Switch Cas, Switch Castiel, Switch Dean, Switch Dean Winchester, Top Cas, Top Castiel, Top Dean, Vibrator, butt plug, doctor cas, human cas
Language: English
Status: Completed
Published: 2014-11-18
Updated: 2014-11-18
Packaged: 2018-02-26 03:16:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2636009
Author URL: https://archiveofourown.org/users/WinterWolf610/pseuds/WinterWolf610
Summary: <blockquote class="userstuff">
              <p>Dean Winchester just spent the night in a sex club with his smoking hot boyfriend, Dr. Castiel Novak, who promised a round two back at his swanky downtown condo. Once they get there, Cas leads Dean into his private sex room and they make good use of it.</p><p>Sequel to Lucky Number Seven but can be read as a stand alone.</p>
            </blockquote>





	Up All Night to Get Lucky

Dean Winchester couldn't sit still. He was in the passenger seat of his beloved 1967 Chevy Impala, with his hot boyfriend Dr. Castiel Novak at wheel. He normally never let anyone drive his baby but he didn't think himself capable of driving safely right now. Dean wasn't drunk per se, at least not on alcohol, but with the butt plug nestled against his prostate, each bump in the road was definitely a distraction. Even though Dean had met Cas because of a car crash, he wasn't planning on getting in another one anytime soon. 

As he stole a look at his angel, the doctor who had saved his life, Dean couldn't help but notice a not-so-angelic smirk on his boyfriend's face. They were stopped at a red light so Cas turned to look longingly at Dean. 

"You're enjoying this way too much," griped Dean. "I think I spoke too soon when I called you an angel."

Cas chuckled. "Having you all on edge, cursing every bump in the road, hungrily eyeing my cock while I drive your precious baby-of course I'm enjoying it. The only way it could be better is if..." Cas trailed off and he reached his left hand into his pocket. Dean faintly heard a click before he began cursing and squirming. The butt plug was a vibrator controlled by a remote in Cas's pocket. 

"Son of a bitch!" Dean cried out. It was too much with the plug pressed up against his prostate and he was going to come all over himself and his perfectly maintained car until the vibrations suddenly stopped. He looked over at Cas with murder in his eyes. "I am so getting you back for this," he promised. 

"I look forward to it, Winchester." Cas smoothly pulled in a parking space in front of his building. He locked Dean in an intense stare before casually remarking, "I'm going to love watching you walk with that plug in your ass. All my neighbors are going to know that you're mine with the way you're already so bowlegged." And with that he got out of the car before Dean could make a snappy comeback.

Dean took a moment to unbuckle his seatbelt and recall how he'd gotten himself in this particular predicament. They'd been seeing each other for a while now but they hadn't been going on proper dates lately and so for their seventh date, the devious angel had invited Dean to meet him at a club, neglecting to mention that it was a sex club that liked to have both professionals and amateurs showcase their kinks and skills in the bedroom. 

After watching the show, Dean was so enthralled with it that he had Cas make arrangements for them to be a part of it. His boyfriend gave them the stage names of Big D & his Angel and his supposed angel had then set about claiming him in front of that whole crowd, and finally slipping a plug between his cheeks and promising a round two in private. He quickly cleaned and dressed them both and carried Dean bridal-style out to the Impala, which Dean had been too blissed out to be embarrassed about at the time. Cas had taken a cab there, which was just as well, because Dean was in no state to drive right then.

That whole experience felt surreal but Dean was going to be fantasizing about it for the rest of his life. A sharp rap on the window knocked him out of his reminiscence. "Don't tell me you've got stage fright now, Big D," taunted his angel outside, turning away towards the door of his building, smirking.

Cursing soundly as he got up and the plug shifted inside him, Dean hurried as best he could after Cas, already plotting his demise. Thankfully, they didn't encounter any of Cas's neighbors on their way up to his condo. Waiting for Cas to unlock his door, Dean realized he was already rock hard and all Cas had done was push his buttons, literally. 

They'd had sex at Cas's place dozens of times before and Dean was certainly eager to get inside so he could get Cas inside him. As Cas currently lived alone, he'd done the rooms however he liked. To Dean's surprise the first time he'd been over Cas had told him the guest bedroom was off limits. Unsure if that was a serious warning or a hopeful hint to stay the night with Cas in the master bedroom, Dean didn't think much of it at the time, until he came over the day after they'd had sex for the first time at Dean's apartment.

The guest bedroom was a sex dungeon. There really was no other way to describe it. The carpet was plush and comfortable to kneel or lay on. A massive luxe four poster bed with soft pillows and clean white sheets and soft shackles attached to the corners of the bed dominated the room. All manner of sex toys and lubes were mounted on the wall and filling up the shelves and ledges about the room. A chest full of role play props sat next to a regal, throne-like chair that could easily support two people without tipping over stood in one corner opposite the bed. A sex swing was set up in the other. A stripper pole had been put in the middle of the huge room. 

There were no windows in this room but it connected to a private bathroom with a luxury shower. It was pale marble like the rest of the room, with a huge ledge seat, glass doors and handholds all over. The removable shower head had a massage setting that had Dean moaning under its hot spray whenever he used it. A huge sunken tub that was more of a jacuzzi made of the same marble as the rest of the bathroom sat on the other side of the shower. It fit two with comfortable room to move around and it was another place Dean loved to unwind in. Being a mechanic was physically demanding work and he and Cas were pretty vigorous in the bedroom so it was nice to let the hot water of Cas's shower or tub run over his tired limbs. The rest of the room was an elegant porcelain throne with a heated seat and matching marble basin under a massive ornate mirror that gave a perfect view of the shower. 

This was the bedroom Cas had steered them into and pressed Dean up against the dull red wallpaper of while kissing him breathless. _"Yup," thought Dean, "My boyfriend is secretly a kinky bastard."_ But if Cas was a kinky bastard, so was Dean. He may not have the resources of a doctor's salary to make his own sex dungeon, but he certainly enjoyed playing in Cas's. He'd been with a few guys before but he'd never been in a committed enough relationship with one to explore this side of himself with. Any exploring of kinks he'd done was a little light domination with women who wanted that sort of thing. His relationship with Cas wasn't really like that.

With Cas he could trade off the responsibilities of the bedroom. Sometimes Dean would be in charge, other times Cas. It was far more rewarding than having to be the one in charge all the time. Some days he could lie back and let Cas take care of him, some days he'd take charge of them both, but most days they battled for dominance, doing their best to outdo each other and push themselves to new heights. 

Dean let out a shameless moan as Cas began to suck a bruise along a tendon in his neck. Dean tightened his grip on his angel's shoulder and hip, urging Cas on with his body. Cas smirked when he came up for air but renewed his ministrations with greater vigor. Thank goodness his work jumpsuit would cover most of the bruise. Dean was sure it would last for a week. His coworkers at the garage would tease him and congratulate him on scoring with some feisty girl. If only they knew...

Cas pulled up and smiled at Dean. "Still with me, Big D, or did I tire you out?" Dean growled softly at him. 

"You know I'm ready for more," Dean growled, pressing his clothed erection against his angel's hip to punctuate his point, "Just thinking about how you bring out my kinkier side. If you told me a year ago that I'd be performing in an amateur live sex show with a smoking hot dude, I would have laughed my ass off."

Cas smiled wolfishly at his lover. "But you rather did enjoy yourself, didn't you? You loved having all those people watching as I claimed you. You looked so good split open on my cock. I wonder how many people there would have liked to trade places with either of us."

"I'm not sharing," growled Dean. 

Cas leaned in close to whisper in his lover's ear, "No, but even you yourself couldn't help but imagine yourself in place of most of the performers, did you not? You loved the threesome between those men and I saw you watching those two women. You'd love for me to strip you down, put you in a cockring, push you down on your hands and knees, strap you to the table so you can't move, open you up with increasingly larger toys, whisper in your ear just like this until you beg for mercy, beg for my cock, beg for your release and you won't be satisfied until I give it to you." Those sinful lips were brushing the shell of his ear as they whispered the dirty words to him. Dean shivered. 

"That sounds real good, except for one thing. I don't beg, angel," whispered Dean back, pushing his boyfriend away gently. 

"Want to bet?" teased his angel devilishly, putting his hands in his pockets. Dean heard the vibrations before he felt it. Once he did, it hit him like a brick wall. He forgot the damn remote to the vibrating butt plug was in Cas's pockets. The so-called angel pinned Dean's wrists above his head, limiting Dean's options to try to relieve the sensations he was feeling. He squirmed and bit his lip, not wanting to give Cas the satisfaction of hearing Dean moan from his dirty little trick. 

Dean looked into Cas's eyes and was startled a bit by the purely predatory gaze he was met with. Cas was just going to let him come untouched in his pants to prove a point. And if Dean let him do that, he was going to be too sensitive for whatever else Cas had planned for tonight. Unless Dean gave in and begged him not to. It was going to be one of those nights. 

But Dean had an idea. He quickly flipped them and turned around with Cas's arms locked to Dean's chest so Cas was unable to move and could feel vibrations against his cock too. Payback was starting now. 

Cas cursed and tried to break his hold but Dean was stronger than him. Cas growled and squirmed. "Fuck, get off. I'll turn it off. Jesus!" Dean let up and the vibrations stopped. They started at each other, panting. It was game on. Cas pounced on Dean, the remote flying from his hand as he did so. They toppled to the soft carpet and Dean ended up on top. Cas reached around and smacked Dean's ass, causing his to clench around the plug still nestled inside him. He howled but didn't lose focus on unbuttoning Cas's shirt as he continued to spank Dean. Dean moaned and ground his crotch against Cas's. 

"Too many layers. How did you manage to get everything back on?" demanded Dean. Cas doesn't deign to answer as he's sucking another mark into Dean's skin and his hands have wandered to Dean's buttons, which he undoes far more deftly than Dean did with his. They shrug out of their shirts and Cas out of his undershirt. Dean runs his hands over Cas's bare chest and Cas unfastens Dean's slacks and pulls down his boxers enough to free his straining erection. 

"Feeling adventurous tonight, Dean?" queried Cas as he gently stroked up and down Dean's hot length. 

Groaning softly, Dean looked down at Cas and moves to cup his face in his hands. "I let you take me to a sex club and publicly have your wicked way with me and I didn't even know I had an exhibitionist kink. I'd say I'm definitely feeling adventurous."

Cas grinned. "Well, I have teased you a lot tonight. A cock ring might prolong our activities tonight. There's a whole collection there on the shelf." Cas gestures to a built in shelf along the wall. Dean gets up off Cas to kick off the rest of his clothes and examine them. It's an impressive collection of rings of various sizes and materials. Some clearly fit around the balls while others were for the shaft or both. Dean picks up a black rubber one and raises an eyebrow as he turns to Cas, who is standing behind him. 

"Just how many men have used these?" He tried to sound nonchalant about it but he knew he failed. He didn't like thinking about Cas inviting other men into this room. 

Cas chuckled and put a hand on Dean's shoulder as he looked him straight in the eye. "Still jealous? As much planning as went into this room, you're the first person I've ever invited in here. I've spent some time alone in here so if things in here have been used, it's been by me and me alone. Until you, I haven't found anyone special enough to bring in here. As you probably know, it's difficult to find someone to trust with your desires." 

Dean nodded. He did know. "Alright, angel. Help me with this?" he asked, handing over the ring. He'd flagged a bit, thinking about Cas with other people but Cas didn't seem to mind. He planted a kiss on the tattoo on Dean's chest and got on his knees to tease Dean's dick a bit to get it rock hard again. Pressing soft kisses and taking little kitten licks along his length had Dean sufficiently hard in no time. Cas stretched the ring and brought it down to rest at the base. Cas took one last lick at his slit, causing Dean to inhale sharply. 

Cas got his feet and caged Dean against the shelf. "What should I do with you now, Mr. Winchester?" purred his angel in that gravelly voice of his. Cas's index finger tilted up Dean's chin so Cas could suck a little mark under his jawbone. Dean let out a soft moan and Cas's other hand wandered behind him to tease the plug still nestled between his cheeks. 

Dean steered Cas to sit in the chair in the corner while he straddled him. Cas was moving the plug just barely in and out and Dean was moaning wantonly at the pleasurable sensations. He busied himself sucking his own marks onto Cas's neck and undoing the fastenings of his pants. He took Cas's cock in hand and stroked leisurely, making sure to rub his slit and massage his pubic bone occasionally. 

Cas's hand coming to his neck and pulling him down into a rough and claiming kiss stopped Dean's movements. "Bed. Now," growled Cas as he broke the kiss. Dean hopped up and waggled his still plugged ass as he made his way to the bed. Cas removed the rest of his clothes and watched Dean move hungrily. 

"How do you want me, angel?" Dean said as he lay seductively on his side in the middle the bed. Cas growled possessively in response.

"I want you in every way, Dean. I want to ruin you for anyone else. We'll start with you on your back in the middle of the bed-grab your knees and hold them up by your head," commanded Cas. Dean complied and Cas circled the bed once before joining him. Cas moved so he was on his hands and knees before Dean, lustily eyeing Dean's plugged hole and ringed cock. 

"Finally," mutters Dean as Cas removes the plug. He blows gently into Dean's gaping hole, causing his lover to curse and shudder. He sticks a finger to gage how wet he was. The lube and come from earlier were still locked inside but Cas wasn't satisfied with that. He grabbed a bottle of lube off the side table and slicked Dean even more. Dean could feel it running down his crack and watched as Cas slicked himself up again. 

Dean licked his lips as he watched Cas get in position to breach him. He was glad he and Cas got tested together because he loved the feeling of sex with Cas without condoms. It was hot to think of whichever one of them had bottomed keeping a bit of the other locked inside. Cas eased his tip inside before looking up to lock eyes with Dean. As he did so, he slammed home. Dean was still loose from their earlier session so he needed no time to adjust. Cas lifted Dean's hips to meet his thrusts as he set a brutal pace and Dean could feel his balls slapping against Dean's slick ass. Dean was moaning with each snap of his lover's hips. He was glad he agreed to a cockring or he might be begging right now. 

Cas was changing pace. He slowed and leaned forward to capture Dean's lips. He pulled all the way out before pushing back in as deep as he could, causing both of them to moan deeply when Cas bottomed out. Dean clenched, making himself tighter and trying to bring Cas to orgasm. From the sounds he was making, Dean was succeeding. 

"Oh, fuck, baby. You feel too damn good," growled out Cas, "I'm going to come. Fuck!" His pace grew erratic before finally sheathing himself fully to spend his load inside his boyfriend. He collapsed forward, rearranging Dean so they could lay side by side, panting from exertion. 

"Damn," panted out Cas, "I wanted to use you more. And you're still hard."

"Well, there are a couple different solutions for that," snarked Dean, not unkindly.

"Mmm, think, mmm, I can arrange something," said Cas between kisses. He had clambered up to Dean's chest and was rubbing up his arms until Dean heard one click and then another. 

"You bastard!" exclaimed Dean upon realizing Cas had cuffed him to the bed and shaking his chains menacingly. 

"Trust me, babe. Please," begged Cas as he stood. Dean sighed and relaxed his body as Cas shackles his ankles to the bed. "Give me a minute." He disappeared into the bathroom, leaving Dean hard and spread eagle on the bed.

Hoping Cas wouldn't be long, he looked around the room to see what exactly Cas had at his disposal to use on Dean. Dildos, vibrators, fleshlights, paddles, floggers, scarves, feathers, blindfolds, gags, plugs, ropes, cock rings, handcuffs, and spreader bars were visible about the room. Dean looked toward the role play chest. He had not actually looked in there yet and began to imagine what sort of fetishware was in there. The whole room and joining bathroom were already fetish made real. Dean would deny it later but he whimpered as he could feel the pleasure coiled in his loins ready to unleash as soon as the ring was off. His mind was too good at imagining the other sorts of things that could happen in this room.

The door of the bathroom opened and Dean turned to look at his boyfriend. He didn't look much different but he was always gorgeous. He was half hard, Dean noticed, as he strode purposefully back to the bed. In seemingly a single motion, he mounted Dean, straddling him and sinking himself down on his sizable cock, moaning as he took Dean in, stopping once he was sitting down and Dean was fully sheathed inside of him. He'd been opening himself up in the bathroom to surprise Dean and accommodate Dean's impressive cock. 

Cas was still adjusting but he began to swirl his hips to pleasure Dean. Dean moaned appreciatively and tried to sit up enough to kiss his angel, who got the hint and met him halfway. He broke the kiss to begin moving up and down Dean's length. He was moaning louder than Dean was. He kept adjusting the angle to try to find his prostate. Once he did, he pursued it with abandon, moaning pornographically as he rode Dean. He started stroking himself with one hand as he brought himself to a second orgasm, splattering all over them both. Cas hopped off Dean and pulled the ring off, taking the head of Dean's cock into his mouth as he shot his load, Cas greedily lapping up what he couldn't swallow in the first go. With all that teasing and build up, Dean's orgasm was powerful and he was still shaking from it. 

Cas unshackled him and his limbs fell limply to the bed. Dean kissed his angel deeply when he came to lay next to him, tasting himself on Cas's tongue. Dean mentally thanked his lucky stars for Castiel, the man who saved his life and raised him up and showed him the joys of a passionate, committed relationship. 

Cas curled up and placed his head on Dean's chest, utterly spent. They both pressed soft kisses onto whatever skin they could reach and Dean wrapped Cas up in his arms. "I love you, Castiel Novak, with all my heart," declared Dean quietly. 

Brightly blue eyes looked warmly up at him. "And I you, Dean Winchester." They both had big, dopey smiles as they moved in for another kiss. Cas pulled away to ask Dean sincerely, "Will you move in with me?" He looked at his boyfriend earnestly, waiting for his reply. 

"Nothing would make me happier, angel," replied Dean smiling. 

"Good. Let's go get cleaned up. Last one in the shower has to do the laundry!" cried Cas as he took off towards the bathroom laughing.

"You cheating cheater that cheats!" called out Dean as he raced after him. "I'm so going to get you!" laughed Dean as he joined his boyfriend in the shower. 

Dean Winchester was a lucky man.


End file.
